"Turpentine Finance" with Sasha Orloff | Startup Finance, Leadership, CFO Strategy

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"Turpentine Finance" with Sasha Orloff | Startup Finance, Leadership, CFO Strategy

A podcast where Sasha Orloff talks to CFOs, founders, and finance leaders at the best tech companies about what it takes to architect success. Our guests speak candidly about big business inflections, market curveballs and how they approach decision-making to tease out tactics and mental models you can use for when the pressure is on. You’ll hear stories from Instacart, Mercury, OpenAI, Andreessen Horowitz, Netflix, Runway, and more. Topics frequently touched upon M&A, Market Downturn, Macro, PMF, Fundraising, Financial Forecasting, Headcount, Equity. Turpentine Finance is part of the Turpentine podcast network. Learn more: turpentine.co

  1. Paul Barnhurst (The FP&A Guy) on What CEOs Want from FP&A

    31 OCT

    Paul Barnhurst (The FP&A Guy) on What CEOs Want from FP&A

    In this episode of Turpentine Finance, host Sasha Orloff sits down with Paul Barnhurst, a passionate FP&A educator and content creator who shares insights on financial planning & analysis, teaching methodologies, and the evolution of financial tools. For full show notes, visit: https://highlightai.com/share/1823b417-abe8-49bb-8f00-d673e24077b1 -- 📰Be notified early when Turpentine drops new publication: https://www.turpentine.co/exclusiveaccess  -- SPONSOR: 🌎ANROK is the enterprise-grade solution that automates sales tax compliance worldwide. Anrok tracks your exposure, calculates tax, and handles filings—all in one platform. Visit https://www.anrok.com/turpentine to claim your free nexus study and take control of your SaaS tax strategy. 💳 Imagine total control over your company's spending with Rippling Spend, the all-in-one platform for expense reports, corporate cards, and bill pay. Control spend, set custom approval chains, and close your books 3x faster. Visit https://www.rippling.com/turpentine for a free demo and one month free trial. -- LINKS: The FP&A Guy: https://www.thefpandaguy.com/ https://www.linkedin.com/in/TheFPandAGuy/ -- X/SOCIAL: @sashaorloff

    50 min
  2. Bootstrapped to $640M: Brad Wiskirchen on M&A, Board Management, and Decision-Making

    24 OCT

    Bootstrapped to $640M: Brad Wiskirchen on M&A, Board Management, and Decision-Making

    In this episode, host Sasha Orloff interviews Brad Wiskirchen about his journey with Kount, the AI-driven fraud prevention company he bootstrapped and sold to Equifax for $640 million, while sharing insights from his experience as a founder and now a partner at CVC Capital Partners. For full show notes, visit: https://highlightai.com/share/eec1be56-ae04-4afc-bb24-7ed8523b2176 -- 📰Be notified early when Turpentine drops new publication: https://www.turpentine.co/exclusiveaccess  -- SPONSOR: 🌎ANROK is the enterprise-grade solution that automates sales tax compliance worldwide. Anrok tracks your exposure, calculates tax, and handles filings—all in one platform. Visit https://www.anrok.com/turpentine to claim your free nexus study and take control of your SaaS tax strategy. 💳 Imagine total control over your company's spending with Rippling Spend, the all-in-one platform for expense reports, corporate cards, and bill pay. Control spend, set custom approval chains, and close your books 3x faster. Visit https://www.rippling.com/turpentine for a free demo and one month free trial. -- LINKS: Kount: https://kount.com/ https://www.linkedin.com/in/bradwiskirchen/ -- X/SOCIAL: @sashaorloff @KountInc

    56 min
  3. Airbase CFO Aneal Vallurupalli on Acquisitions, the Chief “Friction” Officer, and Spend Management

    17 OCT

    Airbase CFO Aneal Vallurupalli on Acquisitions, the Chief “Friction” Officer, and Spend Management

    In this episode, Sasha Orloff is joined by Aneal Vallurupalli, CFO at Airbase, who drops insights on modern spend management and his journey from M&A to leading finance at a Paylocity acquisition target. Aneal discusses his career trajectory, the impactful role of a CFO in spend management, and how Airbase revolutionizes non-payroll spends in the AI era. Aneal also offers essential advice to CFOs navigating today’s dynamic financial landscape. 🔥 Apply to join over 400 Founders and Execs in the Turpentine Network: https://www.turpentinenetwork.co/ -- SPONSORS: ANROK is the enterprise-grade solution that automates sales tax compliance worldwide. Anrok tracks your exposure, calculates tax, and handles filings—all in one platform. Trusted by Notion, Anthropic, and Vanta. Visit https://www.anrok.com/turpentine to claim your free nexus study and take control of your SaaS tax strategy. -- LINKS: Airbase: https://www.airbase.com/ -- X/SOCIAL: @sashaorloff @AVallurupalli -- TIMESTAMPS: (00:00) Preview (01:16) Intro (01:43) Meet Aneal Vallurupalli, CFO of Airbase (02:28) Understanding Airbase's spend management (04:33) Aneal’s journey to Airbase (08:08) Evolution and impact of Airbase (09:43) Role and strategy as CFO (17:34) Sponsor: Anrok (18:59) Balancing flexibility and control in spend management (21:36) Importance of change management (23:58) Memorable customer success stories (27:35) Evolution of software in the CFO's office (31:21) Trends in selling to different industries (37:08) Future of Airbase and business spend management (39:36) Insights on M&A and career journey (43:37) Reflections on buy-side and sell-side experiences (45:39) Wrap

    48 min
  4. Architecting a Global Marketplace for M&A with Flippa CEO Blake Hutchison

    10 OCT

    Architecting a Global Marketplace for M&A with Flippa CEO Blake Hutchison

    In this episode, Sasha Orloff sits down with Blake Hutchison, CEO of Flippa, the leading platform for buying and selling online businesses. Blake shares insights from his career (Xero, Lonely Planet, Good44), and explains how Flippa operates as the ‘investment bank for the 99%,’ providing a marketplace for subscale business transactions. The episode dives into the opportunities presented by the marketplace, key deal characteristics, and the different buyer segments. They also discuss the importance of financial literacy for subscale businesses, provide tips for first-time buyers, and offer predictions for the future of flipping businesses. 🔥Apply to join over 400 Founders and Execs in the Turpentine Network: https://www.turpentinenetwork.co/ -- RECOMMENDED PODCAST: 🎙️ This Won't Last - Eavesdrop on Keith Rabois, Kevin Ryan, Logan Bartlett, and Zach Weinberg's monthly backchannel. Apple Podcasts: https://podcasts.apple.com/us/podcast/id1765665937 Spotify: https://open.spotify.com/show/2HwSNeVLL1MXy0RjFPyOSz -- SPONSORS: RIPPLING Imagine total control over your company’s spending with Rippling Spend, the all-in-one platform for expense reports, corporate cards, and bill pay. Control spend, set custom approval chains, and close your books 3x faster. Visit https://www.rippling.com/turpentine for a free demo and one month free trial. ANROK is the enterprise-grade solution that automates sales tax compliance worldwide. Anrok tracks your exposure, calculates tax, and handles filings—all in one platform. Visit https://www.anrok.com/turpentine to claim your free nexus study and take control of your SaaS tax strategy. -- LINKS: Flippa: https://flippa.com/ https://www.linkedin.com/in/blakehutchison/ -- X/SOCIAL: @sashaorloff @Flippa -- TIMESTAMPS: (00:00) Preview (01:20) Intro (02:26) Blake's career journey (03:37) Flippa: The investment bank for the 99% (05:55) Focus on digital assets (07:20) Selling and buying on Flippa (14:20) Buyer types and market dynamics (18:30) Sponsors: Rippling | Anrok (21:22) Investing in digital assets (26:28) Navigating the first-time buyer market (28:05) Buyer intent and market trends (33:47) Common deal breakers in business sales (36:46) Financial literacy and cloud accounting (44:27) Future trends in online business flipping (47:47) Getting started with Flippa (49:02) Wrap

    52 min
  5. Why Finance Software is About to Change, with Sapphire Ventures' Jane Lee and Aditya Reddy

    3 OCT

    Why Finance Software is About to Change, with Sapphire Ventures' Jane Lee and Aditya Reddy

    In this episode, Sasha Orloff welcomes Jane Lee and Aditya Reddy of Sapphire Ventures to unpack their paper, “Rise of the Next Gen CFO,” which features a market map of CFO tools and identifies key trends and predictions. Jane and Aditya discuss how finance roles are transforming, the convergence of finance and data science, the influence of AI, and emerging investment strategies in this fast-paced sector. Nothing presented within this podcast is intended to constitute investment advice, and under no circumstances should any information provided herein be used or considered as an offer to sell or a solicitation of an offer to buy an interest in any investment fund managed by Sapphire Ventures (“Sapphire”). Information provided reflects Sapphires’ views as of a time, whereby such views are subject to change at any point and Sapphire shall not be obligated to provide notice of any change. No assumptions should be made that investments or strategies described were or will be profitable. Due to various risks and uncertainties, actual events, results or the actual experience may differ materially from those reflected or contemplated in these statements. Nothing contained in this podcast may be relied upon as a guarantee or assurance as to the future success of any particular company or strategy. Past performance is not indicative of future results. -- SPONSORS: ANROK is the enterprise-grade solution that automates sales tax compliance worldwide. Anrok tracks your exposure, calculates tax, and handles filings—all in one platform. Visit https://www.anrok.com/turpentine to claim your free nexus study and take control of your SaaS tax strategy. NETSUITE: More than 40,000 businesses have already upgraded to NetSuite by Oracle, the #1 cloud ERP bringing accounting, financial management, inventory, HR, into ONE proven platform. Download the CFO's guide to AI and Machine Learning at https://netsuite.com/102 METAVIEW is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/heretics OMNEKY is an omnichannel creative generation platform that lets you launch hundreds of thousands of ad iterations that actually work customized across all platforms, with a click of a button. Omneky combines generative AI and real-time advertising data. Mention "Cog Rev" for 10% off https://www.omneky.com/ -- LINKS: Rise of the Next Gen CFO: https://sapphireventures.com/blog/rise-of-the-next-gen-cfo-the-evolution-of-finances-role-and-tech-stack/ Sapphire Ventures: https://sapphireventures.com/ -- X/SOCIAL: @sashaorloff @leejane09 @adityareddy97 -- TIMESTAMPS: (00:00) Preview (00:53) Intro (01:18) Viral market map by Sapphire Ventures (02:23) Rise of the Next Gen CFO (06:25) Key findings from the paper (10:57) Impact of AI on finance (18:09) Sponsors: Anrok | Netsuite (20:36) Complexities with crypto assets (24:22) AI affecting different industries (28:22) Investment insights from Sapphire Ventures (34:58) Sponsors: Metaview | Omneky (36:27) Platform risks (41:06) Sapphire Ventures' focus (43:37) Wrap

    46 min
  6. What Separates Good From Great Treasury, with Eugene Spevakov

    26 SEPT

    What Separates Good From Great Treasury, with Eugene Spevakov

    In this episode, Sasha Orloff is joined by Eugene Spevakov, the Treasurer and Head of Corporate FP&A at 6sense, treasury expert, and veteran CFO. Sasha and Eugene dive deep into the Treasury function: how it differs across industries, how a scaling startup will know when it’s time to hire for the role, how to structure the function, and what separates a great treasurer from merely good. Eugene offers a masterclass on leveraging treasury to drive growth, improve cash flow, and allocate risk strategically in an uncertain world. 🔥Apply to join over 400 Founders and Execs in the Turpentine Network: https://www.turpentinenetwork.co/ -- RECOMMENDED PODCAST: 🎙️ This Won't Last - Eavesdrop on Keith Rabois, Kevin Ryan, Logan Bartlett, and Zach Weinberg's monthly backchannel. Apple Podcasts: https://podcasts.apple.com/us/podcast/id1765665937 Spotify: https://open.spotify.com/show/2HwSNeVLL1MXy0RjFPyOSz -- SPONSORS: ANROK is the enterprise-grade solution that automates sales tax compliance worldwide. Anrok tracks your exposure, calculates tax, and handles filings—all in one platform. Visit https://www.anrok.com/turpentine to claim your free nexus study and take control of your SaaS tax strategy. NETSUITE: More than 40,000 businesses have already upgraded to NetSuite by Oracle, the #1 cloud ERP bringing accounting, financial management, inventory, HR, into ONE proven platform. Download the CFO's guide to AI and Machine Learning at https://netsuite.com/102 METAVIEW is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/heretics OMNEKY is an omnichannel creative generation platform that lets you launch hundreds of thousands of ad iterations that actually work customized across all platforms, with a click of a button. Omneky combines generative AI and real-time advertising data. Mention "Cog Rev" for 10% off https://www.omneky.com/ -- LINKS: https://www.linkedin.com/in/eugene-spevakov-cfa/ 6sense: https://6sense.com/ -- X/SOCIAL: @sashaorloff -- TIMESTAMPS: (00:00) Preview (00:49) Intro (01:14) Understanding treasury (02:22) Meet Eugene Spevakov: A treasury expert (03:39) Basics of treasury functions (05:40) Real-world treasury challenges and risks (09:12) Industry-specific treasury insights (14:07) Sponsors: Anrok | Netsuite (16:30) Treasury in software companies (22:32) Risk management and allocation (27:29) Sponsors: Metaview | Omneky (28:58) When to hire a treasury professional (30:07) Understanding and managing business risks (32:40) Challenges and solutions in treasury functions (37:08) Role and excitement of treasury (43:12) Tools and resources for treasury management (47:40) Advice for building a treasury function (50:32) Wrap

    53 min
  7. The ROI of Storytelling: Camille Ricketts (ex-Notion, FRR, Tesla)on Content as a Business Driver

    19 SEPT

    The ROI of Storytelling: Camille Ricketts (ex-Notion, FRR, Tesla)on Content as a Business Driver

    In this episode, Sasha Orloff sits down with Camille Ricketts, former Co-Head of Marketing at Notion, Editor of First Round Review and Elon’s comms manager at Tesla, to talk about the ROI of content as a growth driver. Camille, currently a partner at XYZ Venture Capital, played a key role in persuading Sasha years ago to invest in content as a revenue channel. In this episode she shares her invaluable insights from her roles at Notion, Tesla, and First Round Review. Tune in to hear Camille’s compelling arguments for CEOs and VPs about the strategic value of content marketing. This is a must-listen for founders, finance leaders, and anyone eager to leverage content for growth. 🔥Apply to join over 400 Founders and Execs in the Turpentine Network: https://www.turpentinenetwork.co/ -- RECOMMENDED PODCAST: 🎙️ This Won't Last - Eavesdrop on Keith Rabois, Kevin Ryan, Logan Bartlett, and Zach Weinberg's monthly backchannel. Apple Podcasts: https://podcasts.apple.com/us/podcast/id1765665937 Spotify: https://open.spotify.com/show/2HwSNeVLL1MXy0RjFPyOSz -- SPONSORS: NETSUITE: More than 37,000 businesses have already upgraded to NetSuite by Oracle, the #1 cloud financial system bringing accounting, financial management, inventory, HR, into ONE proven platform. If you're looking for an ERP platform, get a one-of-a-kind flexible financing program on NetSuite: https://netsuite.com/102 METAVIEW is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/heretics BRAVE: Get first-party targeting with Brave’s private ad platform: cookieless and future proof ad formats for all your business needs. Performance meets privacy. Head to https://brave.com/brave-ads/ and mention “Turpentine” when signing up for a 25% discount on your first campaign. Omneky is an omnichannel creative generation platform that lets you launch hundreds of thousands of ad iterations that actually work customized across all platforms, with a click of a button. Omneky combines generative AI and real-time advertising data. Mention "Cog Rev" for 10% off https://www.omneky.com/ -- LINKS: https://www.linkedin.com/in/camillericketts/ XYZ: https://www.xyz.vc/ -- X/SOCIAL: @sashaorloff @camillericketts -- TIMESTAMPS: (00:00) Episode Preview (00:58) Conversation with Camille Ricketts (02:11) Camille's journey at Notion (04:34) Content as a measurable growth strategy (12:00) Effective use of testimonials and case studies (15:45) Case studies and emotional engagement (17:54) Sponsors: Netsuite | Metaview (19:41) Measuring content success (24:25) Tactical tips for effective call to action (26:08) Figma and Stripe (27:37) Founding story of First Round Review (30:30) Sponsors: Brave | Omneky (31:52) Iterating content formats and overcoming fear (37:04) Role of AI in content creation (42:57) Insights from Tesla and preparing for the unexpected (47:24) Wrap

    51 min
  8. “Founder Mode"? Setting the Record Straight with Jim Cook

    12 SEPT

    “Founder Mode"? Setting the Record Straight with Jim Cook

    When Y Combinator's Paul Graham released his viral essay "Founder Mode," it sparked a firestorm in the tech world. Based on a private talk by Airbnb's Brian Chesky and endorsed by the likes of Elon Musk and Patrick Collison, the piece garnered over 20 million views. Enter Jim Cook, legendary Silicon Valley CFO (Netflix, Intuit, Mozilla) who just wrote a counterargument to set the record straight. Cook challenges the simplistic notion of founder supremacy — where only 10% succeed — and offers a different Leadership Mode framework for building high-performance, generational companies. 🔥Apply to join over 400 Founders and Execs in the Turpentine Network: https://www.turpentinenetwork.co/ -- RECOMMENDED PODCAST: 🎙️ This Won't Last - Eavesdrop on Keith Rabois, Kevin Ryan, Logan Bartlett, and Zach Weinberg's monthly backchannel. They unpack their hottest takes on the future of tech, business, venture, investing, and politics. Apple Podcasts: https://podcasts.apple.com/us/podcast/id1765665937 Spotify: https://open.spotify.com/show/2HwSNeVLL1MXy0RjFPyOSz YouTube: https://www.youtube.com/@ThisWontLastpodcast -- SPONSORS: NETSUITE: More than 37,000 businesses have already upgraded to NetSuite by Oracle, the #1 cloud financial system bringing accounting, financial management, inventory, HR, into ONE proven platform. If you're looking for an ERP platform, get a one-of-a-kind flexible financing program on NetSuite: https://netsuite.com/102 METAVIEW is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/heretics BRAVE: Get first-party targeting with Brave’s private ad platform: cookieless and future proof ad formats for all your business needs. Performance meets privacy. Head to https://brave.com/brave-ads/ and mention “Turpentine” when signing up for a 25% discount on your first campaign. Omneky is an omnichannel creative generation platform that lets you launch hundreds of thousands of ad iterations that actually work customized across all platforms, with a click of a button. Omneky combines generative AI and real-time advertising data. Mention "Cog Rev" for 10% off https://www.omneky.com/ -- LINKS: Cook’s Playbooks https://jcookflix.substack.com/ Founder Mode PG https://paulgraham.com/foundermode.html Lenny’s Podcast episode with Brian Chesky https://www.youtube.com/watch?v=4ef0juAMqoE Product-CEO Paradox by Ben Horowitz https://a16z.com/why-founders-fail-the-product-ceo-paradox/ Hard Thing About Hard Things by Ben Horowitz https://a16z.com/books/the-hard-thing-about-hard-things/ Scaling People with Claire Hughes Johnson https://www.goodreads.com/book/show/63063173-scaling-people -- X/SOCIAL: @sashaorloff @cookflix -- TIMESTAMPS: (00:00) Episode preview (00:26) Intro (00:51) Founder Mode essay (04:13) Challenges of polarized arguments (07:44) Importance of leadership mode (10:59) Balancing founder and scaling modes (15:01) Sponsors: Netsuite | Metaview (16:49) Trust and transparency in leadership (20:41) Importance of creating a culture (24:57) Leading with values and behaviors (29:48) Sponsors: Brave | Omneky (31:13) Importance of documentation (36:45) Balancing founder and manager roles (39:06) Structuring ownership and accountability (43:06) Founders as Coaches and Captains (48:12) Specialized operators in finance (50:41) Scaling company to public (53:50) Wrap

    58 min
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About

A podcast where Sasha Orloff talks to CFOs, founders, and finance leaders at the best tech companies about what it takes to architect success. Our guests speak candidly about big business inflections, market curveballs and how they approach decision-making to tease out tactics and mental models you can use for when the pressure is on. You’ll hear stories from Instacart, Mercury, OpenAI, Andreessen Horowitz, Netflix, Runway, and more. Topics frequently touched upon M&A, Market Downturn, Macro, PMF, Fundraising, Financial Forecasting, Headcount, Equity. Turpentine Finance is part of the Turpentine podcast network. Learn more: turpentine.co

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